4-pentadecyl-1H-imidazol-2-ylamine | 1111393-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-pentadecyl-1H-imidazol-2-ylamine
• 英文别名: 5-pentadecyl-1H-imidazol-2-amine
• CAS: 1111393-47-5
• 化学式: C₁₈H₃₅N₃
• 分子量: 293.496
• InChiKey: KRQAOOSQUTZGQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氨基咪唑硫酸盐 、 4-pentadecyl-1H-imidazol-2-ylamine 在 N-氯代丁二酰亚胺 、 盐酸 作用下， 以 甲烷磺酸 、 甲醇 为溶剂， 反应 48.0h， 以6%的产率得到5-(1-(2-amino-1H-imidazol-4-yl)pentadecyl)-1H-imidazol-2-amine hydrochloride
  参考文献：
  名称：

  Using Small-Molecule Adjuvants to Repurpose Azithromycin for Use against Pseudomonas aeruginosa

  摘要：

  A major contributor to fatalities in cystic fibrosis (CF) patients stems from infection with opportunistic bacterium Pseudomonas aeruginosa. As a result of the CF patient's vulnerability to bacterial infections, one of the main treatment focuses is antibiotic therapy. However, the highly adaptive nature of P. aeruginosa, in addition to the intrinsic resistance to many antibiotics exhibited by most Gram-negative bacteria, means that multi-drug-resistant (MDR) strains are increasingly prevalent. This makes the eradication of pseudomonal lung infections nearly impossible once the infection becomes chronic. New methods to treat pseudomonal infections are greatly needed in order to eradicate MDR bacteria found within the respiratory tract, and ultimately better the quality of life for CF patients. Herein, we describe a novel approach to combatting pseudomonal infections through the use of bis-2-aminoimidazole adjuvants that can potentiate the activity of a macrolide antibiotic commonly prescribed to CF patients as an anti-inflammatory agent. Our lead bis-2-AI exhibits a 1024-fold reduction in the minimum inhibitory concentration of azithromycin in vitro and displays activity in a Galleria mellonella model of infection.

  DOI：

  10.1021/acsinfecdis.8b00288